Aluminium lithium hydride → (5-Bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol

HRID 1876402Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:13](OC)=[O:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][OH:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (668) (466 mg, 1.63 mmol) in tetrahydrofuran (16 mL) at 0° C. was added LAH (1 mL, 1.96 mmol). The reaction was stirred at 0° C. for 1 hour and quenched with 0.2 mL of water, 0.2 mL of 15% NaOH and 0.6 mL of water. The reaction was warmed to room temperature and diluted with diethyl ether. Magnesium sulfate was added and the solution was filtered, washed with diethyl ether, and the solvent removed in vacuo to provide (5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol (669).

Workup

customquenched with 0.2 mL of water, 0.2 mL of 15% NaOH and 0.6 mL of water
temperatureThe reaction was warmed to room temperature
additiondiluted with diethyl ether
additionMagnesium sulfate was added
filtrationthe solution was filtered
washwashed with diethyl ether
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-1c6b43d2ddb44ce9a36bd6dd343520e6
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309600B2

Reaction notes

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